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Outlook unable to connect and sync with exchange server

Posted on 2009-04-22
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Oultlook 2007 unable to connect and sync with exchange server 2003.  Cisco VPN shows connected and working properly.  I'm able to access network resources.  Outlook shows trying to connect then changes to a status of disconnected after a minute.  Only one user is experiencing this problem.    
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Question by:bkeating13
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Expert Comment

by:esmith69
ID: 24208592
You may need to modify your HOSTS file to include an entry that maps to the Exchange server.  I would try this first and see if it fixes it.  If not, there are other things you can try.
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by:bkeating13
ID: 24208664
Can you give me an example of the HOSTS file entry?
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Expert Comment

by:esmith69
ID: 24208711
just put the IP address of the Exchange server, then press TAB, then enter the host name of the Exchange server.  Then save the file.  Make sure it doesn't add .txt to the end of the file--the HOSTS file should have no file extension.
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Expert Comment

by:Mestha
ID: 24209273
While HOSTS file will work, it is a poor answer. You should avoid using HOSTS file where possible. People forget they are there and then when something changes find that things do not work. I have inherited two networks with hosts files and removed them all, and deployed four networks using the Cisco VPN client (including my home network) and was able to use Outlook over all of them. Hosts files are not required.

Does name resolution work for the Exchange server over the VPN connection? Try and ping the Exchange server by all three combinations of IP address, netbios and FQDN. It should resolve to the internal IP address. If it comes back with an external address then name resolution isn't working correctly.

If it is only one user then it has to be something with their specific machine. Is it location dependant?

Simon.
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Author Comment

by:bkeating13
ID: 24209480
I will have the user try pinging as you suggested.  Not sure what you mean by location dependant.  The user is part of the domain that the Excahnge server is on.  It is a small network of 25 users.
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Expert Comment

by:Mestha
ID: 24209718
By location dependant I mean if the user goes somewhere else with their VPN connection, does it work in a different location?

Simon.
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Author Comment

by:bkeating13
ID: 24209791
He has had problems from at least 3 different locations.  He has tried from home, hotel and wireless air card.  All three pings timed out.  I am sending him a new VPN profile file.
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Expert Comment

by:esmith69
ID: 24209799
the HOSTS file method is not a permanent fix (unless you want it to be) but it is a quick and easy way to help narrow down where the problem is occuring.  At least if the HOSTS file works, then you know it is a DNS resolution issue.
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Author Comment

by:bkeating13
ID: 24216153
Here is the result of an IPCONFIG from the users computer.  Could the Microsoft Loopback Adaptor be causing the problem?  

Microsoft Windows XP [Version 5.1.2600]
(C) Copyright 1985-2001 Microsoft Corp.
C:\Documents and Settings\jcameron>Ipconfig /all
Windows IP Configuration
        Host Name . . . . . . . . . . . . : jim
        Primary Dns Suffix  . . . . . . . :
        Node Type . . . . . . . . . . . . : Hybrid
        IP Routing Enabled. . . . . . . . : No
        WINS Proxy Enabled. . . . . . . . : No
        DNS Suffix Search List. . . . . . :
Ethernet adapter Local Area Connection 6:
        Connection-specific DNS Suffix  . :
        Description . . . . . . . . . . . : Microsoft Loopback Adapter
        Physical Address. . . . . . . . . :
        Dhcp Enabled. . . . . . . . . . . : No
        IP Address. . . . . . . . . . . . : 10.10.0.10
        Subnet Mask . . . . . . . . . . . : 255.255.255.0
        Default Gateway . . . . . . . . . :
Ethernet adapter Local Area Connection 2:
        Media State . . . . . . . . . . . : Media disconnected
        Description . . . . . . . . . . . : Intel(R) 82567LM Gigabit Network Con
nection
        Physical Address. . . . . . . . . :
Ethernet adapter Local Area Connection 5:
        Connection-specific DNS Suffix  . :
        Description . . . . . . . . . . . : Novatel Wireless Ovation EV-DO Netwo
rk Adapter
        Physical Address. . . . . . . . . :
        Dhcp Enabled. . . . . . . . . . . : Yes
        Autoconfiguration Enabled . . . . : Yes
        IP Address. . . . . . . . . . . . : 75.220.91.187
        Subnet Mask . . . . . . . . . . . : 255.0.0.0
        Default Gateway . . . . . . . . . : 75.220.91.1
        DHCP Server . . . . . . . . . . . : 75.220.91.1
        DNS Servers . . . . . . . . . . . : 66.174.95.44
                                            66.174.92.14
        Lease Obtained. . . . . . . . . . : Wednesday, April 22, 2009 3:59:04 PM
        Lease Expires . . . . . . . . . . : Saturday, April 25, 2009 3:59:04 PM
Ethernet adapter Local Area Connection 3:
        Connection-specific DNS Suffix  . :
        Description . . . . . . . . . . . : Cisco Systems VPN Adapter
        Physical Address. . . . . . . . . :
        Dhcp Enabled. . . . . . . . . . . : No
        IP Address. . . . . . . . . . . . : 192.168.248.144
        Subnet Mask . . . . . . . . . . . : 255.255.255.0
        Default Gateway . . . . . . . . . :
        DNS Servers . . . . . . . . . . . : 192.168.248.10
        Primary WINS Server . . . . . . . : 192.168.248.10
C:\Documents and Settings\jcameron>
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esmith69 earned 1500 total points
ID: 24216544
That is a bit interesting that the loopback adapter has an IP assigned to it (other than 127.0.0.1).

Have you tried modifying his HOSTS file yet?  That will at least help narrow down where the issue is occurring.
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